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Personally, I started as a bird dog and then wholesaler in the single-family home business.

Please email me at my personal email if you have time to chat - need people in my area to offer guidance and suggestions.

Absolutely do contact Yonah, he is the best person to answer your cost seg questions.As far as determining feasibility, it is usually done by your tax accountant who can estimate your immediate and future tax savings.

How would you pay the person if this is part-time help?

@Bradley Elrod  if you  rent to a family member at below market rent it is considered personal use. 

If they need any receipts/invoices, those are all in their portal.I personally would keep a spreadsheet to double-check numbers.

You need to seriously consider ditching this person and replacing them with a pro!

Very frustrating when I qualify for a HELOC but its getting stopped due to LLC vs my personal name. 

I'm the type of person who needs to be hands-on to learn and understand.